Terpenyl cyanamides



' hl id A preferred equation for t duced pressure. The residue is vacuumdistilled 15 in 150 of heptane- After cooling e 5 hydrochloride isfiltered ofland washed with 25 I .30 heptane. Thawashings and filtrateare united. cyanamma v I The heptane 1S removed y d1s m1at1n underSimilarly other disubstituted cyanamides of rfgduced pressure residue 15vacuum the above classes may be prepared utilizing the t11led and theproduct 1dent1fied as bornyl ethyl corresponding Secondary amine.

cyanamlde' I It is to be understood that the above examples Example Hare illustrative only. 35

' are gradually added with stirring. When this Patented Mar. 19, 1940. I

UNITED STATES PATENT orrics TERPENYL CYANAMIDES I Richard 0. Robli mrJn,Stamford, Conn, assignor to American Cyanamid Company, New York, N. Y.,a corporation. of Maine No Drawing. Application May 23, 1939,

Serial No. 275,222

p v 7 Claims. (Cl. 260-551) v This invention relates to newdisubstituted The benzene is removed by distillation under recyanamidecompounds of the formula duced pressure. The residue is vacuum distilledand the product identified as bornyl phenyl cyanamide. 5 NCN Example IV5 6.1 grams of cyanogen chloride are dissolved wh r 1 representsterpenyl radical in 200 cc. of benzene. After cooling the solutionrepresents a radical chosen from the group conto w grams of fenchylphenyl amine 10 sisting of alkyl, aryl and aralkyl radicals. are dua lyadded w t stirring; W this 10 Thes compounds may b generally preparedaddition is completed, the fenchyl phenyl amine in an inert solvent suchas benzene or petroleum hydrochloride s fi e ed 1f. and Washed Withether fractions, by the reaction between'the corn The washings d fi te ae un tedresponding Secondary amine and cyanogen The benzene is removedby distillation under retion is a follows; 7 I and the productidentified as fenchyl phenyl R R R cyanamlde.

' Example V 6.1 grams of cyanogen chloride are dissolved in 200 cc. ofheptane. After cooling the solution E- p I l to 0-5 C., 48.6 grams offenchyl benzyl amine are gradually added with stirring. When this gramsof cyanogen chlonde aredlssolved addition is completed, the fenchylbenzyl amine non to 0L5) gragms m ethyl amiee heptane. The washings andfiltrate are united. f m d Wlth stlrrmgwhen 111115 The 'heptane isremoved by distillation under readditlon is completed, the bornyl ethyamme duced pressure. The residue is vacuum distilled hydrochlorlde 1sfiltered ofi and Washed with and the product id tifi d as f h l benzyl61 grams of cyanogen chloride are dissolved These new compounds areadapted for varlous uses, more particularly as intermediates, ina c il bi g rains i f i rffi i igfiyfifigg secticides and plasticizers fornatural and synthetic resins. are gradually added wlth StlI'I'lll". Whenthls addition is completed, the fenchyl methyl amine W.h11e the mventlonhas P described wlt.h 40

' hydrochloride is filtered and Washed with particular reference tospecific embodiments, 1t yieptana The washings and filtrate are unitedis to be understood that it is not be limited there- The heptane isremoved by distillation under-re to but is t'o'be construed broadly andrestricted duced pressure. The residue is vacuum distilled solely by theScope of the appended clalms' f l I claim: 45 zg ggg g ldentlfied asenchyl methy- 1. As a newcompound, a disubstituted cyan- Example Inamide of the formula 6.1 grams of cyanogen chloride are dissolved r in200 cc. of benzene. After cooling the solution 50 to 0-5 C., 45.8 gramsof bornyl phenyl amine addition is completed, the bornyl phenyl aminewhere R represents'a terpenyl radical and R hydrochloride is filteredoff and washed with represents a radical chosen from the groupconbenzene. The washings and filtrate are united. sisting of alkyl, aryland aralkyl radicals. 55

2. As a new compound, a disubstituted cyanamide of the formula- NON NON

R! 15 where It represents a terpenyl radical and R represents an arylradical.

4. As a new compound, a. dlsubstituted cyanamide of the formula \NCN R!where R represents a terpenyl radical and R. represents an aralkylradical.

5. As a new compound, bornyl ethyl cyanamide.

6. As a new compound, borny phenyl cyanamide.

7. As a new compound, fenchyl benzyl cyanamide.

RICHARD O. ROBLIN, JR.

